


Doppelgänger (little bird sing)

by Exaggerated_Specificity



Category: Supernatural, Supernatural RPF
Genre: Anal Fingering, Anal Sex, Bottom Jensen, Coercion, Dirty Talk, Dubious Morality, Extremely Dubious Consent, Extremely Underage, Feminization, Implied Dean Winchester/Sam Winchester, Implied/Referenced Incest, Implied/Referenced Underage Relationship(s), Implied/Referenced Underage Sex, Loss of Virginity, M/M, Oral Sex, Painful Sex, Sexual Coercion, Size Difference, Size Kink, Soulless Sam Winchester, Top Sam, Underage Jensen, Underage Sex
Language: English
Status: Completed
Published: 2016-03-27
Updated: 2016-03-27
Packaged: 2018-05-29 04:06:40
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 1
Words: 5,498
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6358690
Author URL: https://archiveofourown.org/users/Exaggerated_Specificity/pseuds/Exaggerated_Specificity
Summary: <blockquote class="userstuff">
              <p>Written for SPN Masquerade Spring 2016. The prompt was: "<i>Soulless Sam sweet talks an underage girl/boy into giving up her/his cherry. As young as you want.</i>" </p>
<p>Soulless Sam has a little fun with one extremely young Jensen Ackles. Read the warnings. This is every bit as dirtybadwrong as it sounds.</p>
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	Doppelgänger (little bird sing)

**Author's Note:**

  * For [saltandbyrne](https://archiveofourown.org/users/saltandbyrne/gifts).



> Original SPN Masquerade post [HERE](http://spn-masquerade.livejournal.com/7665.html?thread=2689521#t2689521). Tumblr post [HERE](http://exaggeratedspecificity.tumblr.com/post/141760652508/doppelg%C3%A4nger-little-bird-sing).

The grass is blissfully cool under Sam’s back as he repositions his arm to shield his eyes from the afternoon sun. He’s been waiting nearly forty-five minutes for the guys at Monro Muffler and Brake to finish the tune-up on his Charger but at least he wasn’t stuck in the cramped waiting room next to the elderly woman in a mumu who smelled like week-old coffee and cat piss. It’s hot as balls even though it’s nearly October but the picnic table on the corner next to the garage is the only shade close enough to hear the rumble of the car’s engine when they pulled it around once it was done. It should only be another ten minutes or so and then Sam would be back on the road, good as new.

“Hey, isn’t that the little fag from gym class? Jensen or whatever?”

The boys are far enough away that Sam doesn’t notice them until the word ‘ _fag_ ’ pricks in his eardrum like a thorn. Three clones of varying heights in baseball caps, crisp blue jeans, and bright white sneakers are walking down the sidewalk. Rich kids, cocky as the day is long, with no sense of self-preservation. The same kind of jock assholes that seemed to be fixtures at every school in the lower forty-eight. 

“Yeah, that’s him. Jensen Ackles,” one of them snorts, saying the unusual name like it’s a dirty word.

Sam pushes up on his elbows and sees a young blonde kid waiting at the city bus stop right in front of his patch of green. The boy’s slight back is to Sam but he can see the freckles speckling the back of his neck and the way it’s flushed extra pink from the sun. The seemingly older boys are further down the block, coming closer as they continue hurling insults.

“S’up, Jenny? You waiting for your boyyyfriendddd? Fucking queer.” One of them barks. As they get closer Sam realizes these punks don’t even look old enough to be in middle school. He’d forgotten how young shit like this started. 

Sam watches on coldly, an exercise in observation more than anything else. He remembers when something like this would have make his skin crawl, made his own cheeks flush as pink as Jenny’s neck, only with righteous anger instead of sunshine. These days he’s not so… emotional. 

“He’s in my English class too, fuckin’ know-it-all, always spoutin’ off Shakespeare and shit.”

“Aw, that’s cute. A faggot _and_ a nerd! Tell me, bro. Are you the Romeo or the Juliet in the relationship?”

“Come on, just look at him! Definitely Juliet. Pretty pink lips just like a fuckin’ girl’s. Bet you suck a lotta cock, dontcha, Ackles?” 

Sam’s interested enough to stand now but the kids are too involved in their after-school harassment to notice his muscular, imposing frame. 

“What’s the matter, fag? That’s right, you’re a fuckin’ FAG, huh?”

Sam looks on as the Ackles boy turns his head to glare at the bullies. The kid doesn’t say a word. It’s clear they want a fight but he’s not playing, he tightens the straps on his backpack and looks up the street, eager for his bus to come. 

The boys edge closer, fanning out like a pack of rabid dogs ready to attack. They’re not satisfied with the silence of their target. Sam had seen this kind of thing all too regularly during his own childhood. He may be too removed from that entire part of his life these days to truly empathize but, if there’s one thing he hates, its monsters. These boys were much more likely to grow into a fine set of them if he let their sick taunts continue. 

He steps from the grass onto the sidewalk, crossing his arms over his broad chest. 

“So what if he's a fag?” Sam says, his deep voice catching all three of the little hooligans off guard. “What if I'm a fag, too? You gonna beat us both up?” 

He’s practically twice the height of even the tallest of the trio. The look on their faces is priceless as they evaluate Sam, the interloper, their eyes wide, mouths hanging open. 

“Get the fuck out of here,” Sam growls, stomping his right boot on the concrete just to watch them jump. 

He can see the baby fat jiggle in their cheeks as their faces flush with panic. The ringleader buries his hands in his pockets and shoves past Jensen to continue down the block. The other two follow behind like good little lap dogs and just like that it’s quiet again in the blazing afternoon sun. 

Jensen stands there quietly, his head tipped down, his narrow shoulders folding in a little like he’s trying to hide standing right there in the open.

“Ignore those pussies,” Sam says, his voice as gentle as he can make it. “At least one of them is gonna go home after this and beat off to the pictures in his Boys’ Life Magazine. Guaranteed.” 

Sam steps up right next to the kid, tilting his head to the side to try and give him a smile but the boy’s eyes are closed, his sweet little face is pinched up, and there are tears wetting his long eyelashes. Sam reaches out to put his hand on the boy’s shoulder, a reassuring gesture, something he does out of sense memory more than anything. He’s nearly knocked backwards as Jensen opens his big, teary green eyes and looks at Sam. His face is the spitting image of a _very_ young Dean Winchester.

“Jesus fuck,” Sam gasps, gripping the boy like it’s the only thing holding him upright. 

“Thanks,” Jensen offers weakly, his plump bottom lip quivering as a tear slips down his round cheek. “Sorry, y-you didn’t have to do that, I – I can take care of myself…”

“Christ, you’re…” Sam breathes, a lifetime of memories rush through his mind with the speed of a bullet train, the images of his brother blurring, dizzying. This kid is Dean’s doppelganger and it brings Sam as close to having a real feeling as he’s been in months. It’s bizarre and exhilarating. 

Jensen looks confused, his eyes darting over to Sam’s hand that’s still clamped protectively over his bird-boned shoulder. 

“Shit, sorry,” Sam says, releasing his grip. He can’t pull his hand away without wiping a tear from Jensen’s cheek with his thumb. “You just – fuck, you look exactly like someone I haven’t seen in a really long time. Someone that meant a whole lot to me. Just surprised me is all. I’m Sam, Sam Winchester.”

Sam crams his hand in his pocket so he doesn’t run his thumb over the kid’s lower lip. He takes a deep breath and shakes his head, trying to pull himself out of whatever nostalgic delirium he’s lost in. Looking at the love of his life’s mini-clone had knocked him on his ass. Sam’s cock twitches in his jeans as he clears his throat.

"Anyway, like I said, don’t let what those kids were saying get to you too much, Jensen. Alright?”

The boy nods, his lips parted a little, his tears drying up. He’s staring up at Sam the way Sam always used to gaze at Dean. Like he hung the fucking moon. 

“You know, people used to tell my brother he had cock-sucking lips too and he grew up really big and strong.” 

“Wow, like, as big and strong as you?” Jensen says, his voice full of awe and his eyes wide, roaming over Sam’s chest and biceps without a hint of shame. 

“Yeah, yeah he did. Well, almost,” Sam grins, unable to resist as Jensen lights up, his face so round and pretty it practically hurts Sam to look at him. Little heartbreaker. “Listen, Jensen. I know you’re waiting for your bus and all but my car is in the shop right over there. It’s gonna be ready here any minute. I can give you a ride home, if you want.”

“Can’t, mom’s working ‘til late,” Jensen sputters as his cheeks pink up, his words blurting out too quickly, forced. “I take a bus to the YMCA, they have after-school camp…” Jensen looks less than enthusiastic about going to the Y, shrugging his shoulders as his face falls. “She’s a nurse, she works a lot…” 

“Hey, I know what that’s like. My dad worked all the time when I was a kid. Left me and my brother alone a bunch. It gets lonely…” 

As if on cue, Sam hears the chrome-rumble of the Charger’s engine revving off in the distance. It pulls him from the stare job he can’t seem to stop giving Jensen’s mouth. Christ, he’s just a baby, but Sam was already doing filthy, horrible things to his big bro back when he was Jensen’s age, maybe it wasn’t such a stretch.

“Hear that?” Sam asks, motioning toward the garage with his head. “Sounds like my car’s done. I’ll take you wherever you want to go,” Sam offers again, watching as sweat beads up on Jensen’s freckled forehead. “You maybe…” God, he shouldn’t. He _really_ fucking shouldn’t. Sam wasn’t who he used to be but he still knew right from wrong. Didn’t he? “I’m staying in a hotel over by the freeway. There’s a soda machine and air conditioning and free HBO. We could hang out until your mom gets off her shift?” 

Excitement floods Jensen’s eyes as quickly as the tears had earlier but he tucks his thumbs under the straps of his backpack and looks down at his feet, sighing hard enough to make his shoulders bob up and down.

“No, I get it. Stranger danger and all that. You’re right. You’re a smart kid. Seem like a real good boy. Wouldn’t want you to do anything to get in trouble with your mom.”

Sam needs to stop watching ‘ _To Catch A Predator_ ’ reruns, insomnia or not.

Jensen looks up, his brow knit in conflict. Sam can see that he wants to say yes as clearly as if there were a sign pinned to his faded t-shirt. The loud hiss-screetch of hydraulic breaks makes Sam look up from Jensen’s face. The boy hears it too, looking back over his shoulder at the lumbering, crowded bus pulling up to the curb at the stop across the intersection. 

“That’s my bus…” He says softly before looking down at the toes of his scuffed Chuck Taylor’s again. He looks back up at Sam, a serious expression painted across his precious, delicate face. “You’ll take me to the Y before my mom gets off work at eight, right, Sam? Promise?”

“Scout’s honor,” Sam says, raising his hand in the air like he was being sworn in to testify in court. He sticks with it even though he’s pretty sure it’s three fingers or something but Sam had a hunter’s life instead of a sash full of patches. Jensen doesn’t care, he smiles big at Sam and nods, pushing up on his toes.

“Okay, yes. Let’s go.”

Jensen just made Sam the closest to _happy_ he’s been in the better part of a year.

~

Jensen is a lot chattier on the drive to the hotel than he’d been at the bus stop baking under the Texas sun. He opens to Sam up in a way that says he probably doesn’t have a strong male role-model in his life. That on top of being grateful to Sam for saving his skin has clearly impaired Jensen’s pre-teen judgement.

Jensen’s cocktail of eager, young, damaged, and gorgeous is pushing Sam’s buttons in ways that only Dean had ever been able to, the Dean who gave Sam every single one of his firsts. It was like a time machine had picked Sam up and dropped him back in 1987, thrumming with pent-up desire and lacking a moral compass. 

The Motorlodge parking lot is blissfully empty as Sam pulls the Charger in front of his room. He keeps an eye out as he ushers Jensen inside, getting him settled on the king-sized bed with the TV remote before venturing out for ice, an armful of sodas, and a pile of candy from the vending machines near the office. 

There was apparently an ‘ _Indiana Jones_ ’ marathon on whatever premium channel Jensen had flipped the crappy TV to and when Sam gets back he’s sitting on the bed cross-legged and barefoot in his holey jeans and well-worn Spurs t-shirt like Sam’s dirtiest wet dream. 

Sam dumps the candy on the bed in front of Jensen and sets the ice bucket full of sodas down on the night stand, slipping his hand into the drawer for the KY he’d stashed there the night before. 

“Sweet, I love Red Vines,” Jensen says, plucking the package from the selection strewn across the bed as Sam cranks up the AC unit under the window. He pulls the curtains closed and smiles at Jensen. 

“There, is that better? Easier to see, right?” Right….

Jensen shrugs, kicking his legs out in front of him as he takes a bite of red licorice, chewing happily as Sam moves the other candy onto the night stand next to the sodas. He sets to taking off his boots and peeling off his socks, casually stripping out of his shirt in the process and using it to wipe the sweat off his neck and from under his armpits. 

“Fucking hot in Texas,” he says matter-of-factly, winking back at Jensen over his shoulder. He can feel the boy’s eyes on him – curious, maybe a little awe-struck. Sam’s like ninety-nine percent sure Jensen’s never seen a grown man naked, much less one Sam’s size. He’s more in shape than he’s ever been in his life, tan and rippling like some kind of Grecian hero, a monster slaying machine. If things went the way they seemed to be, he might have to commit suicide. Sam shrugs at the thought before settling back against the headboard next to Jensen. He’d make sure it was worth it.

They watch the movie and drink a full soda each, Sam a Dr. Pepper and Jensen an A&W Cream Soda. Sam remembers Short Round shouting “Dr. Jones!” when he chases the sweet, creamy taste of it with his tongue, kissing Jensen until he’s shaking and breathless. 

“You’re being such a good boy, Jensen,” Sam whispers as he kisses up the side of the boy’s sweaty neck, nipping right under his ear, just enough to make him whimper a little, his fists balling up in the cheap comforter. 

“Did that feel good?” He asks, not really caring what the answer is. “You taste so good.” 

Sam licks up the tendon at the side of Jensen’s neck, pausing to suck briefly right over his pulse point. He licks the salty-sweet from his lips, his dick already rock fucking hard for this kid. Jensen’s heart is racing when Sam slides his hand up the line of his slender leg, over his knee, fingertips questing up his inner thigh. 

“Do you want me to stop?” Sam asks soft and breathy, right up against Jensen’s ear as his big hand cups the boy’s entire crotch. Jensen’s breath catches in his throat, his red vine colored tongue slipping out to wet his bottom lip, but he doesn’t say a word. “Good. That’s good, Jensen. I really don’t wanna stop.”

Sam works Jensen’s jeans open one handed. He was always better at that then unhooking bras thanks to Dean’s tutelage. 

“You ever play with yourself, Jen?” Christ, he’s already using pet names. He was gone for this kid. Gone as Dean ever was for his Sammy. “Yank on this pretty little dick? Make yourself come?” 

Jensen’s jaw quivers as he nods a weak ‘ _yes_ ’ for Sam. He’s just a baby, probably doesn’t even get the mechanics of it all yet. No dad at home to give him a proper sex talk – not the kind a nurse would give – the kind about making yourself feel really good. It’s okay, Sam was an excellent teacher, just like Dean had been.

Sam’s on his knees, blocking the TV now, but Jensen’s eyes are on him and not the movie as he tugs Jensen’s jeans and boxers down in one smooth motion. Jensen’s eyes are wide, his pupils blown in the dim hotel room, and his little cock is standing straight up even if the rest of the kid’s body seems paralyzed with fear. He helps Jensen tug off his t-shirt before kissing him again, one hand braced against the bolted-in headboard and the other running down Jensen’s chest, making goosebumps race down his arms, making his tiny pink nipples hard.

Sam pulls away from Jensen’s mouth, his fat bottom lip trapped between Sam’s teeth for one final tug before he sets on moving south, down, down, down, until he’s got the boy’s cock between his lips, tongue sweeping over it. Tastes a million times better than any sugary sweet from the vending machine. Sam groans around it, the flavor of little-boy precome a distant but vivid memory, one ingrained so deep he swears it’s in his DNA. This was the next logical progression without his real brother nearby to satisfy him. That’s what he tells himself, anyway.

Sam only knows Jensen comes from the high-pitched, strung-out sounds he makes and the way his little body tenses up from head to toe under Sam’s much larger one. His cocklet barely leaks a trickle but he feels Jensen’s bare little balls seize up against his chin. Sam opens his mouth wider to fit them inside too. He keeps mouthing at Jensen’s genitals until Sam can only taste his own spit, until his tiny dick is nothing but a floppy toy for Sam’s over-zealous tongue.

Sam settles back down next to Jensen with a happy hum, wrapping his arm around the boy’s waist, and pulling him close. He nuzzles up against the side of Jensen’s neck and rocks his hips closer, letting his hard on rut against Jensen’s thigh through his jeans.

“Was that okay, Jensen?” Sam asks, forcing sincerity and concern into his tone. He’s hard enough to cut glass and, while he truly hopes Jensen is having fun, at this point he’s going to keep going even if the kid starts to cry. He might even like it more than he’s ready to admit if he actually did.

“Y-yes…” Jensen mumbles, his heart still racing. Sam can feel it. 

“Good, I’m glad. You’re being a very good boy for me. The absolute best. But you know what I want to try?”

“Hm?” Jensen manages, looking into Sam’s eyes as he strokes his long fingers through the boy’s sun-streaked hair. 

“Well,” Sam says softly. “I made you feel good, right? So I thought maybe you could try to make me feel good too. I mean, that’s fair, don’t you think?”

Jensen nods, holding the eye contact and biting his lip a little. Sam can tell Jensen isn’t quite sure what that means even though he seems to react pretty positively to the praise. 

“That's right. That's what a good boy would do. And you’re a VERY good boy, Jensen.”

Sam settles back on the bed, resting his back up against the headboard with his legs stretched out in front of him. 

“What do you think? Think your mouth would look pretty wrapped around this?" Sam slides his hand from where it’s resting on his knee up between his spread thighs, cupping the bulge of his cock, and giving it a firm squeeze. Jensen’s eyes follow his hand and he licks his lips subconsciously. It makes Sam’s dick lurch uncomfortably against the inside of his zipper. “Do you wanna see it, Jensen? See what a real man’s cock looks like?”

That’s what makes Jensen finally look away, eyes darting to the floor as his cheeks go an even deeper pink under that pretty sea of freckles. 

“It’s okay to be curious. No one else will ever know,” Sam reassures as he thumbs open the button on his jeans. 

“Just kiss it a little, just like I did for you, and we can stop whenever you want. Okay, Jenny?" 

Jensen does his best once Sam’s jeans are off, abandoned in a pile on the floor. He climbs between Sam’s long legs and gives him a breathy little whine as Sam press his thumb into the divot underneath his bottom lip, holding his jaw open to push the angry purple head of his prick inside. 

Sam’s leaking so much that his precome is seeping out of the side of Jensen’s mouth after just a few clumsy sucks. It feels better than fucking heaven. He even likes it when Jensen’s sharp little canine teeth drag over him. He has to reach down to grip the base of his cock hard and rough to keep from unloading right then and there. 

“You know what else good boys do to make men feel good, Jensen?” Sam asks, meeting Jensen’s eyes as he does his best to suck Sam deeper. He manages to shake his head, the little muffled sound in his throat tells Sam that Jensen has very little idea. Anatomy books aren’t the best resource when it comes to getting fucked. 

The boy’s lips are bright red and puffy when he eases Jensen off his cock, like he’d just eaten a cherry popsicle too quickly. He shakes his head again, dipping his chin down a little like he’s embarrassed for not knowing. 

Sam pulls Jensen up into his lap, stroking his hair again. “I can put it inside you, Jen. Push it in so it’s way up here, right in your belly.” Sam slides his palm over the pale, pudgy slip of Jensen’s stomach, his prick throbbing as his hand eclipses the kid’s entire stomach. “That would make me feel even better than you using your mouth. It would be a real nice way to pay me back for letting you come over, for making you feel good before. Should we try it?” Sam tips his head forward, forcing Jensen to meet eyes. “Show me what a good boy you can really be?”

Jensen’s thighs are so delicate under Sam’s big, calloused hands, so pliable. Sam perches Jensen’s plush little ass on his knees, his hand rubbing slow and gentle up and down Jensen’s thigh as he reaches over and grabs the KY off the nightstand. 

“I’m gonna get it real slick with this stuff. It’ll help it go in, make it easier to fit.” 

Jensen’s eyebrow quirks a little, as skeptical as he should be, but his eyes stay locked on Sam’s erection. He lubes it up slow, focusing most of the thick gel on the tip where there’d be the most resistance. 

“Is – is it gonna hurt a lot?” Jensen asks, the bright, talkative boy from the car ride over is long gone. “it’s – it’s so much bigger… than mine.”

“Yeah, I’m not gonna lie to you, kiddo,” a line straight from the lips of Dean Winchester. “It’s gotta go in right here,” he coos, rubbing two of his thick, lubed up fingers between Jensen’s bouncy little ass cheeks. “Gonna give me your cherry and that always hurts, but only for a little while. I promise.” Sam circles his fingertips over Jensen’s insanely tight pucker. “But, I’m gonna make you a deal. You get to be in control, okay? Just like before, we can stop whenever you want. So, if it hurts too much, we can stop. You’ll be on top. Here,” Sam pulls Jensen forward, coaxing him onto his knees before guiding Jensen’s hand back to grip Sam’s shaft. His hand feels so fucking small, it barely makes it all the way around Sam’s girth. 

“I’ll guide it in. Just hold it steady and try to push out against it, like when you’re on the toilet.” 

Jensen’s face is pinched with concentration, like Sam has given him some complicated maneuver he’s trying to memorize. It’s not going to fit, Sam didn’t even get a finger in the kid yet, but it was going to be so much fun to watch him try. With a (fake) gentle smile, Sam pulls Jensen forward with one hand and guides the lubed up head of his erection up snug against his asshole with the other. 

“Push, baby. Try to sit on it, try to let me in.” 

His slit is leaking like a faucet and there’s so much lube it’s practically a joke, the hard, too-thick head of his dick slip-slides over Jensen’s virgin boy hole just like it would if he was rutting up into his armpit. There might as well not be any opening there at all. Still, Sam likes the look of stern concentration on Jensen’s face and the way he’s got his little fist wrapped around the base of his cock, trying his hardest to get Sam inside. 

Sweat starts to bead up on Jensen’s forehead just like it had when they were out in the afternoon sun and he’s grunting, whimpering, his face red from trying to push Sam’s impossible girth up into his virgin cunt. Sam strokes his back, showers him with praise and encouragement, and does his best to hide the wicked smile on his face when little tears start glistening in the corners of Jensen’s big, green doe eyes.

"We can stop if you want, Jenny. It’s okay.” It’s not. 

“There's lots of other boys I can find who can take it. Promise, it’s okay, just like I said. We’ll stop." Sam gives the kid a lazy smile, pleased when he sees the desperation on his sweet face. 

"No, no, please, Sam, I can! It's just - it's j-just so big." Jensen’s voice gets a little higher, he’s rambling, and it sounds like he might start to cry.

“Hey, hey, what if we try something else?” Sam soothes. “How about I do the pushing this time? You know I’m real strong, I bet I could get it in.”

Jensen bites his bottom lip and nods, those spring-green eyes so wide, so eager to please. Even if they were glistening with fresh tears.

“Okay, beautiful boy,” Sam says as he moves Jensen over on the bed next to him, positioning him on his hands and knees and sliding one of the pillows under his head. “Keep your butt in the air, okay? You can grab onto the pillow and rest your head on it but you have to keep your ass in the air. That’s the only rule. Be a good boy, arch that pretty back for me.” 

Sam slides his hand down the curve of Jensen’s lower back, coaxing his shoulders to the bed but keeping his other hand locked firm on his hip. 

“Spread your legs, baby. Show me your hole. We’ll get it open, don’t worry.” 

God, that pink little furl nearly makes Sam come as soon as he gets his eyes on it. It’s going to be so tight it’ll keep Sam from blowing his load too fast, like a built in cock ring. 

He wants to lick it, shove his tongue inside, feast on the taste of little boy ass, but Sam never did like the aftertaste of KY jelly. He would have bought something special for the occasion if he had known he was going to have company. 

He grabs the tube spreads a thick line of it along the first two fingers of his right hand. 

“Take a deep breath for me, Jenny,” Sam says, still stroking the boy’s flank as he pushes the tips of his fingers inside. It’s like a tiny pink vice, the boy’s hole clenches up too-tight around Sam’s thick fingers. Jensen yelps, panting and shaking, looking back at Jared over his shoulder with panicked eyes. 

"Shh, shh. It's okay, Jensen. Just breathe. If you can’t get my fingers in how are you ever gonna take my cock?” 

It would be a miracle if he didn’t rip the boy in half, if he was honest. But Sam wasn’t very honest these days, not when it came to making his dick happy. 

“Hurts –” Jensen whimpers, his voice shuddering, tears ready to flow. 

“I know it does, I told you it would, remember? But you’re my good boy, Jenny. So pretty, so pure. Let me get your little hole opened up. Then you’re gonna make me feel so, so good.” 

Sam shoves in deeper, pressing his other palm between Jensen’s shoulders, pinning him to the bed as he plows in to the knuckle. The kid is crying, without a doubt. Sam is a little worried he’s going to piss off the neighbors once he managed to wedge his dick inside. 

Sam watches the clock as the corkscrews his fingers, thrusting in and out of Jensen’s tight hole, working him open as patiently as he can manage. After five minutes, the sounds Jensen is making are more like the happy little sobs Sam wants than the pathetic cries he’d gotten at the start. 

“You are gorgeous like this, Jensen. So good for me. I’m so proud of you.” 

Jensen moans and bucks back against Sam’s stilled hand, the final gate before Sam pulls his fingers out and lubes up his dick for the second time. He should really get a third finger in, work the kid for another ten or fifteen minutes, but Sam’s dick is a leaking, throbbing mess and he won’t last long as it is. 

“Now, Jensen. This is going to hurt. Are you sure you want me to fuck you?” Sam curls his fingers down, flicking against Jensen’s prostate. The boy yelps, clutching the pillow and shutting his eyes. “Is that a yes?” Sam chuckles as he slides his fingers out. 

Jensen’s hole is puffy and pink as his mouth was when Sam first laid eyes on him earlier that afternoon. He fucks his fingertips in a few more times, watching the tiny little gape it makes when he pulls out. After he’s fucked the boy, it won’t be nearly so pristine and pretty. Sam should really take a picture but his phone’s forgotten somewhere on the floor with his jeans and he’s got a cherry to pop. 

He snugs the head of his dick up against that little pucker and pushes, leaning forward with all his weight and feeding the head inside. He has to slap his hand over Jensen’s mouth to muffle the scream. 

“So fucking tight,” Sam grits out, his hips twitching with restraint. “Come on, Jenny. Gotta let me all the way in. Like a good boy. Breathe through your nose, try and relax this little cunt or else it’ll tear.” 

Jensen is writhing under his weight, whimpering against his hand, a panting, crying sniveling mess as Sam deflowers him. 

He doesn’t remember crying so much the first time Dean fucked him. 

He soothes the boy as best he can, even as he keeps shoving deeper.

“Shh, it’s okay baby, shh. You feel so fucking good, you know that? Feel like fucking heaven around my cock. You can take it, I know you can.” 

It takes a little time but eventually Sam’s entire length is buried deep in Jensen’s guts. The boy pulses and quivers around him as his little body is wracked with sobs. He grinds in deep, keeping his pelvis flush with the kid’s round ass. He could come just like this but it’ll be so much better if he makes a little room for his balls to empty. 

“I’m gonna fuck you now, precious one. Give it up for me, give me that virgin pussy.” 

It only takes a few slow, deep thrusts to get the kid carved out to fit Sam’s dick. He finally releases the grip he has on the base and grabs Jensen’s hips, fucking him in earnest. Jensen’s chewing on his bottom lip, his face red and tear streaked, but he’s taking it so good. God, Sam wished he could fucking keep him.

Sam is pretty sure he comes harder than he ever has. Well, since Dean was around anyway. His balls twitch and spurt after spurt is funneled right up into the kid’s insides, making his thrusts a sloppy, gorgeous mess. 

He pulls out quicker than he’d like, knowing how much it hurts from personal experience. He doesn’t want to fuck the kid up too much. Not yet. It was still early. Plenty of time to make his little bird sing. 

He pulls the trembling boy against his chest, pressing soft kisses all over his head and shoulders. 

“God, Jensen. You made me feel so good. You’re the best, most beautiful boy I’ve ever seen. Thank you.” 

Sam takes a deep breath and closes his eyes, tightening his arms around Jensen in as close to a gentle embrace as he can manage. Sure, he’s a monster. He knows it, he proved it today once and for all. But maybe he’d wait on the suicide for a little while.


End file.
